HIGHLY STRAINED BICYCLIC SYSTEMS .12. SYNTHESIS AND SOLVOLYSIS OF 1,5,5-TRIMETHYLBICYCLO[2.1.1]HEX-2-YL P-TOLUENESULFONATE

被引：34

作者：

MEINWALD, J

SHELTON, JC

BUCHANAN, GL

COURTIN, A

机构：

[1] Department of Chemistry, Cornell University, Ithaca

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1968年 / 33卷 / 01期

关键词：

D O I：

10.1021/jo01265a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1,5,5-trimethylbicyclo[2.1.1]hex-2α-yl p-toluenesulfonate (5) from l-bornyl acetate (6) is described. Acetolysis of 5 results chiefly in the formation of a ring-opened product, 25a. The solvolysis rate shows that significant enhancement results from the presence of the bridgehead methyl group at C1, in accord with positive charge delocalization to this position in the transition state. © 1968, American Chemical Society. All rights reserved.

引用

页码：99 / &

共 24 条

[1] On a new camphor derivative: "Oxo-bornylene". [J].

Asahina, Y ;

Ishidate, M ;

Tukamoto, T .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1936, 69 :355-357

[2] On the oxidation of bornyl acetate. [J].

Asahina, Y ;

Ishidata, M ;

Tukamoto, T .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1936, 69 :349-354

[3] NUCLEOPHILIC REACTIVITY OF CARBON-CARBON DOUBLE BOND .2. SOLVOLYTIC RING CLOSURE OF 2-(3-METHYL- AND 3,4-DIMETHYL-DELTA3-CYCLOPENTENYL)ETHYL P-NITROBENZENESULFONATES [J].

BARTLETT, PD ;

SARGENT, GD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1297-+

[4] P-diketocamphan and the constitution of Schrotter's oxycamphei [J].

Bredt, J ;

Goeb, A .

JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1921, 101 (10/12) :273-292

[5]

BROWN WG, 1961, ORG REACTIONS, V6, P475

[6]

COREY EJ, 1963, J ORG CHEM, V28, P1128

[7]

CRANDALL JK, 1963, THESIS CORNELL U

[8]

ELIEL EL, 1962, STEREOCHEMISTRY CARB, P304

[9]

HART H, 1966, ADVANCES ALICYCLI ED, V1

[10]

HORNER L, 1955, BER, V88, P934

← 1 2 3 →